Simcoe County Vacation Rentals

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Top Cities in Simcoe County

Top Vacation Rentals in in Simcoe County

Our top choices for Simcoe County vacation rentals

SUMMERHILL

2.0 star property
8.0 out of 10, Very good, (2)
"We liked the property a lot"
The price is CA $135
CA $354 total
includes taxes & fees
Sep 13 - Sep 14
SUMMERHILL

Alton Lodges

2.0 star property
7.8 out of 10, Good, (8)
"I love the place ❤️❤️❤️.And the owner is very friendly and easy to communicate. Definitely we will come back again ❤️❤️❤️."
The price is CA $222
CA $353 total
includes taxes & fees
Sep 1 - Sep 2
Alton Lodges

Downtown Collingwood Condos

3.0 star property
9.2 out of 10, Wonderful, (14)
"Very spacious, newly renovated. Wonderful fireplace and tv. Comfortable bed"
The price is CA $147
CA $326 total
includes taxes & fees
Sep 2 - Sep 3
Downtown Collingwood Condos

Margarita Vacation Getaway

3.5 star property
9.2 out of 10, Wonderful, (7)
"Great location, very clean and has everything you need. Bed is very comfortable! Great hosts, with excellent communication! Will stay again. "
Margarita Vacation Getaway

The Nordic -Central Collingwood Condo

3.0 star property
4.0 out of 10, (1)
"It is a shame that third party companies are offering properties with no sole, renting someones home should be an adventure"
The price is CA $123
CA $303 total
includes taxes & fees
Sep 15 - Sep 16
The Nordic -Central Collingwood Condo

Modern Tiny Wood Cottage #3 Camping style Cottages 5 minutes to the beach!

2.0 out of 10, (1)
The price is CA $141
CA $235 total
includes taxes & fees
Sep 4 - Sep 5
Modern Tiny Wood Cottage #3 Camping style Cottages 5 minutes to the beach!

Exquisite Log Cabin Retreat- Perfect Couple’s Getaway! Tranquility at its best❤️

10.0 out of 10, Exceptional, (308)
"A very relaxing and comfortable stay set with the beautiful backdrop of the Blue Mountains."
Exquisite Log Cabin Retreat- Perfect Couple’s Getaway! Tranquility at its best❤️

BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 9

9.2 out of 10, Wonderful, (19)
"I had a wonderful vacation and i will return next year. If you are looking for beachfront this is the place. The small cottage had everything we needed. Thank you..."
The price is CA $225
CA $549 total
includes taxes & fees
Sep 1 - Sep 2
BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 9

Traditional Tiny Wood Cottage #14 Camping style Cottages 5 minutes to the beach!

The price is CA $220
CA $336 total
includes taxes & fees
Aug 31 - Sep 1
Traditional Tiny Wood Cottage #14 Camping style Cottages 5 minutes to the beach!

Carriage Studio Retreat

5.4 out of 10, (3)
"Great location and facilities! Clean and check in process went smoothly. Good communication with property manager. "
The price is CA $110
CA $223 total
includes taxes & fees
Sep 2 - Sep 3
Carriage Studio Retreat

Horseshoe Valley Suites - The Glade

4.0 star property
9.0 out of 10, Wonderful, (9)
"Great place to stay"
Horseshoe Valley Suites - The Glade

Muskoka - The Eagle's Nest

9.6 out of 10, Exceptional, (60)
"Spent a cozy 2 days here, the sunroom grills were amazing!"
Muskoka - The Eagle's Nest

The Georgian Bay Cottage - Hot Tub + Sauna + Fire-pit + More!

10.0 out of 10, Exceptional, (1)
"It was very nice and quiet. Right across the street from a good restaurant which was also nice. "
The Georgian Bay Cottage - Hot Tub + Sauna + Fire-pit + More!

Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage

9.8 out of 10, Exceptional, (6)
"This rental was very affordable with lots of beds. We enjoyed our stay and had plenty of room for a larger group."
The price is CA $127
CA $409 total
includes taxes & fees
Sep 23 - Sep 24
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage

Chic Staycation Condo at FH

7.8 out of 10, Good, (10)
"Amazing stay! It was very beautiful and the place was kept very clean. Had a balcony with seating. Really close walking distance to the boardwalk. Just bring your own shower amenities (ex; body wash)"
The price is CA $130
CA $297 total
includes taxes & fees
Sep 2 - Sep 3
Chic Staycation Condo at FH

Modern Tiny Wood Cottage #0 Camping style Cottages 5 minutes to the beach!

8.0 out of 10, Very good, (3)
"Great staff and experience overall! Will definitely be back!! "
The price is CA $173
CA $275 total
includes taxes & fees
Aug 31 - Sep 1
Modern Tiny Wood Cottage #0 Camping style Cottages 5 minutes to the beach!

Cozy Waterfront Cottage with Pool/Sauna/BBQ/Wifi

10.0 out of 10, Exceptional, (2)
"Amazing location and views. A lot of amenities on the property."
Cozy Waterfront Cottage with Pool/Sauna/BBQ/Wifi

Cozy 2BR Highpoint located at the Friday Harbour

9.4 out of 10, Exceptional, (16)
"Wonderful area and host was very helpful "
Cozy 2BR Highpoint located at the Friday Harbour

Waterfront Muskoka with Hot Tub

9.2 out of 10, Wonderful, (23)
"Great stay. Great host. Be sure to bring your own supplies though because the gas station and convenience stores have a huge markup. Would definitely go back again."
The price is CA $495
CA $897 total
includes taxes & fees
Sep 1 - Sep 2
Waterfront Muskoka with Hot Tub

COZY COTTAGE WALKING DISTANCE TO LAKE SIMCOE & FRIDAY HARBOUR

9.2 out of 10, Wonderful, (48)
"We had a great time. Place was nice and the host was great. Would definetly consider returning if we visit the area again"
COZY COTTAGE WALKING DISTANCE TO LAKE SIMCOE & FRIDAY HARBOUR
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Simcoe County Hotel Reviews

Find out more about Simcoe County

Find out more about Simcoe County

Everything you need to know about Simcoe County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Simcoe County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Simcoe County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Simcoe County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Simcoe County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Simcoe County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Simcoe County vacation rentals we have selected for you start as low as CA $110 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Simcoe County rentals

At Expedia, we put the best Simcoe County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Simcoe County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Simcoe County vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Simcoe County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.